Tetrahydrofuran → HCID 86705505, compound

HRID 2279510Notes

Reaction equation

HRID 2279510 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[O:16][C:17]([F:20])([F:19])[F:18])/[CH:5]=[N:6]/[S@@:7]([C:9]([CH3:12])([CH3:11])[CH3:10])=[O:8].[CH2:21]1COC[CH2:22]1.C([Mg]Br)C>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:5]([NH:6][S@@:7]([C:9]([CH3:10])([CH3:11])[CH3:12])=[O:8])[CH2:21][CH3:22])[CH:13]=[CH:14][C:15]=1[O:16][C:17]([F:20])([F:18])[F:19]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 140626495HCID 140626495, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 86705505HCID 86705505, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 218 (3.8 g, 12 mmol) and THF (40 mL) cooled to −78° C. was added dropwise a solution of ethylmagnesium bromide (5.8 mL, 17 mmol) in ether and the solution was stirred for 1 h, quenched with water, and extracted with Et2O. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (35 to 40% EtOAc) to afford 3.5 g (84%) of (R)—N—((R)-1-(3-chloro-4-(trifluoromethoxy)phenyl)propyl)-2-methylpropane-2-sulfinamide (220).

Workup

  1. customquenched with water
  2. extractionextracted with Et2O
  3. customThe crude product was purified by SiO2 chromatography
  4. washeluting with an EtOAc/hexane gradient (35 to 40% EtOAc)

Sources & evidence

ORD record
ord-219c27629ec94d0da7f95a623597b69a
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

Loading…